1. Route 66 | CA to IL
It would be blasphemous not to include Route 66 at the top of any road trip roundup. The iconic Mother Road is one of the U.S. Highway System’s original routes, starting in downtown Chicago and winding its way across the country to the Santa Monica pier. Covering eight states and approximately 2,500 miles, the historic highway is punctuated with pops of kitsch and classic Americana from a bygone era.
Can’t-miss pit stop: Join a guided tour of the 400-million-year-old Meramec Caverns in Missouri. Jesse James famously used them as a hideout, and the Jesse James Wax Museum is just minutes away.
Trip length: 2,448 miles